WO2001038414A1 - Composition pour adhesif - Google Patents

Composition pour adhesif Download PDF

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Publication number
WO2001038414A1
WO2001038414A1 PCT/EP2000/011576 EP0011576W WO0138414A1 WO 2001038414 A1 WO2001038414 A1 WO 2001038414A1 EP 0011576 W EP0011576 W EP 0011576W WO 0138414 A1 WO0138414 A1 WO 0138414A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
component
resin
polyisocyanate
polyepoxide
Prior art date
Application number
PCT/EP2000/011576
Other languages
English (en)
Inventor
Didier Arnoux
Stuart James Thompson
Original Assignee
Vantico Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vantico Ag filed Critical Vantico Ag
Priority to AU21612/01A priority Critical patent/AU2161201A/en
Publication of WO2001038414A1 publication Critical patent/WO2001038414A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group

Definitions

  • This invention relates to a curable composition based on epoxide/isocyanate mixtures containing specific fillers and to the use of these compositions as adhesives.
  • Typical polymers with potential for demonstrating such high strength properties contain (in small or large extent, depending on the final mixture of properties required) stable, rigidising groups, usually cyclic groups (e.g. poly-p-phenylene, poly-(1 ,4-triazole), polystyrylpyridine etc.). Combination of such rigidising groups with 'interpenetrating networks' to cause further increase in T g has been particularly sought after in recent years.
  • rigidising groups usually cyclic groups (e.g. poly-p-phenylene, poly-(1 ,4-triazole), polystyrylpyridine etc.).
  • U.S. Patent No. 5,494,981 discloses an epoxy-cyanate ester composition that forms interpenetrating networks via a Bronsted acid.
  • the combination of such rigidising groups in a 'inter penetrating network' maybe in a fully or part cured condition, the part cured version maybe stable and then is referred to as a prepolymer.
  • Stable prepolymers containing oxazolidinone and isocyanurate rings can be prepared by reaction of polyepoxides and polyisocyanates in the presence of tertiary amine catalysts.
  • EPIC resins are suitable as casting resins and can be fully crosslinked to yield products having good mechanical properties and, in particular, high heat resistance.
  • WO 93/12170 discloses resin compositions containing a epoxide-isocyanate resin and a metallic filler. These compositions are used as casting resins which are resistant to shrinkage during heating and yield products of high heat resistance and hardness.
  • the present invention relates to a composition
  • a composition comprising
  • Polyepoxides which can be used for the preparation of EPIC resins are relatively low- viscosity aliphatic, cycloaliphatic or aromatic epoxides as well as mixtures thereof.
  • suitable polyepoxides are bisphenol-A-diglycidylether, bisphenol-F- diglycidylether, hydrogenated bisphenol-A-diglycidylether, hydrogenated bisphenol-F- diglycidylether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, polyglycidylether of phenol/formaldhyde novolak or cresol/formaldehyde novolak, diglycidyl esters of phthalic, isophthalic or terephthalic acid, hydantoin epoxy resins, triglycidyl- isocyanurate, triglycidyl-p-aminophenol, tetraglycidyldi
  • compositions according to the invention contain as component (a) a resin wherein the polyepoxide is a diglycidylether or a diglycidylester.
  • polyepoxides are the diglycidylethers of bisphenol A and bisphenol F.
  • Polyisocyanates useful in the compositions according to the invention include low-viscosity aliphatic, cycloaliphatic or aromatic isocyanates and mixtures thereof.
  • Diisocyanates are preferred, in particular diisocyanates of the formula OCN-X-NCO, wherein X denotes a bivalent aromatic, cycloaliphatic or aliphatic-cycloaliphatic radical.
  • polyisocyanates examples include 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexane-1 ,6-diisocyanate, cyclohexane-1 ,2-diisocyanate, cyclohexane-1 ,3-diisocyanate, cyclohexane-1 ,4-diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, isophorone diisocyanate, phenylenediisocyanate, xylene diisocyanate, toluene- 2,4-diisocyanate, toluene-2,6-diisocyanate, naphthalene-1 ,4-diisocyanate, 4,4'-diphenylether diisocyanate, 4,4'-diphenylsulfone diisocyanate, 2,2-bis(4-iso
  • polyisocyanates and mixtures of liquid polyisocyanates with higher molecular polyisocyanates or carbodiimide polyisocyanates can also be applied.
  • Further suitable polyisocyanates are dimers and trimers of the above-mentioned multivalent isocyanates; such polyisocyanates have end-position free isocyanate groups and contain one or more uretdione and/or isocyanurate rings.
  • Particularly preferred polyisocyanates are phenylenediisocyanate, toluene diisocyanate, biphenyl diisocyanate, isophorone diisocyanate, 2,2-bis(4-isocyanatophenyl)propane and diphenylmethane diisocyanate.
  • Diphenylmethane 2,4'-diisocyanate and diphenylmethane 4,4'-diisocyanate are the most preferred polyisocyanates.
  • mixtures of polyepoxides and polyisocyanates can be cured in a two- step process to produce in the first step an intermediate product containing isocyanurate and oxazolidinone rings which is then converted into its final, crosslinked state in the second step by further application of heat.
  • the intermediate prepolymer containing isocyanurate and oxazolidinone rings is storage- stable and can be prepared at ambient or slightly elevated temperatures, preferably up to 50°C, in the presence of catalysts.
  • Suitable catalysts are, for instance, tertiary amines and imidazoles.
  • Preferable tertiary amines include tetramethylethylene diamine, dimethyloctylamine, dimethylamino ethanol, dimethylbenzylamine, 2,4,6-tris(dimethylaminomethyl)phenol, N,N'-tetramethyldiaminodiphenyl methane, N,N'-dimethylpiperazine, N-methylmorpholine, N- methylpipehdine, N-ethylpyrrolidine, 1 ,4-diazabicyclo-(2,2,2)-octane and quinolines.
  • Preferable imidazoles include 1 -methylimidazole, 2-methylimidazole, 1 ,2-dimethylimidazole, 1 ,2,4,5-tetramethylimidazole, 1 -benzyl-2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 1 -cyanoethyl-2-ethyl-4-methylimidazole, 1 -cyanoethyl-2-phenylimidazole and 1 -(4,6-diamino-s-triazinyl-2-ethyl)-2-phenylimidazole.
  • the polyepoxide and polyisocyanate are preferably applied in such amounts that the ratio of epoxy groups to isocyanate groups is in the range of 1 : 1 to 1 : 5, in particular 1.0 : 1.5 to 1.0 : 4.0.
  • the amount of the catalyst is advantageously 0.01 parts by weight to 5.0 parts by weight, preferably 0.25 parts by weight to 2.5 parts by weight, per 100 parts by weight of component (a).
  • component (a) can either be applied as a mixture of a polyepoxide and a polyisocyanate or, preferably, as a prepolymer containing isocyanurate and oxazolidinone rings as part of a polymer network obtained by reaction of a polyepoxide and a polyisocyanate
  • a mixture of low-viscosity EPIC resins with special polyol formulations is used, thus obtaining casting resins with short curing and demolding times.
  • Such compositions are commercially available, e.g. Blendur ® M supplied by Bayer.
  • the prepolymers containing isocyanurate and oxazolidinone rings can be fully cured to crosslinked products by heating the resin to 80-220°C, preferably in the presence of curing catalysts.
  • Suitable catalysts for the crosslinking reaction are the same as those listed above for the formation of the intermediate prepolymers.
  • Silane-treated fillers are known, for example from U.S. Patent No. 4,357,271 , as reinforcing additives for thermoplastic resins.
  • U.S. Patent No. 5,932,625 discloses that inorganic fillers the surface of which is treated with a silane coupling agent can be incorporated in photo- curable resins based on acrylates.
  • Suitable fillers which can be used as component (b) in the compositions according to the invention include inorganic fillers like metals in powder form, metal oxides, hydroxides, carbonates, sulfates, silicates, silica, carbon and glass as well as organic fillers like melamine/formaldehyde resins.
  • fillers are aluminium oxide, calcium hydroxide, magnesium hydroxide, hydrated alumina, titanium dioxide, dolomite, chalk, CaCO 3 , barite, gypsum, talc, mica, kaolin, wollastonite, bentonite, aerosils, quartz, quartz powder, fused silica, glass powder, glass fibres, glass beads, wood flour, carbon black and powders of aluminium, bronze, copper, iron, steel, lead and zinc.
  • component (b) is selected from the group consisting of metal powder, carbon fibres, glass fibres, glass beads, polymer fibres, polymer particles, core/shell polymers and powder additives.
  • Glass beads are particularly preferred.
  • the amount of the filler in the compositions according to the invention is advantageously 30 to 150 parts by weight, preferably 50 to 120 parts by weight, per 100 parts by weight of component (a).
  • the silane according to component (c) is preferably a compound of the formula I
  • R is a monovalent organic group having 2 to 100 carbon atoms, where one or more than one carbon atom can be replaced by O, S, N or Si atoms and where Y,, Y 2 and Y 3 are each independently of one another C ⁇ -C 20 alkyl, C 5 -C 20 aryl, C 5 -C 12 cycloalkyl, C 2 -C 20 -alkoxyalkyl or CrC 2 oacyl.
  • the silanes of formula I are known and can be prepared according to known methods. Some of these silanes are commercially available.
  • Preferred silanes are those of formula I, wherein R defined as monovalent organic group containing 2 to 100 carbon atoms is d ⁇ oalkyl, C 5 -C 2 oaryl, C 6 -C 2 oaralkyl, C 5 -C 12 cycloalkyl, C 2 -C 20 -alkoxyalkyl, C 2 -C 2 oalkenyl, C 4 -C 25 acryloxyalkyl, C 4 -C 25 methacryloxyalkyl, C 2 -C 20 - aminoalkyl, C 4 -C 25 glycidyloxyalkyl, C 7 -C 25 epoxycyclohexylalkyl or the radical of a poly- siloxane.
  • Alkyl defined as R, Y 1 ( Y 2 or Y 3 typically includes methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl as well as the different isomeric pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups.
  • Aryl defined as R, Y ⁇ Y 2 or Y 3 preferably contains 6 to 10 carbon atoms and can be, for example, phenyl, pentalinyl, indenyl, naphtyl, azulinyl and anthryl.
  • Cycloalkyl defined as R, Yi, Y 2 or Y 3 is preferably C 5 -C 8 cycloalkyl, particularly preferably C 5 cycloalkyl or C 6 cycloalkyl. Some examples are cyclopropyl, dimethylcyclopropyl, cyclo- butyl, cyclopentyl, methylcyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • alkoxyalkyl defined as R, Y,, Y 2 or Y 3 are 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl and 3-ethoxypropyl.
  • Alkenyl defined as R typically includes propenyl, isopropenyl, 2-butenyl, 3-butenyl, iso- butenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyi, n-octadec-2-enyl and n-octadec-4-enyl.
  • Typical examples of acryloxyalkyl and methacryloxyalkyl are 2-acryloxyethyl, 2-methacryl- oxyethyl, 3-acryloxypropyl and 3-methacryloxypropyl.
  • Suitable aminoalkyl groups are, for example, 2-aminoethyl, 3-aminopropyl, 3-aminobutyl and 4-aminobutyl.
  • Suitable glycidyloxyalkyl groups can be, for example, 2-glycidylethyl, 3-glycidylpropyl, 3- glycidylbutyl and 4-glycidylbutyl.
  • Epoxycyclohexylalkyl is preferably ⁇ -(3,4-epoxycyclohexyl)ethyl.
  • R in formula I is preferably methyl, ethyl, n-octyl, vinyl, 3-mercaptopropyl, 3-aminopropyl, 3- glycidyloxypropyi, 3-acryloxypropyl, 3-methacryloxypropyl, ⁇ -(3,4-epoxycyclohexyl)ethyl, N- ( ⁇ -aminoethyl)-3-aminopropyl, 3-ureidopropyl, 3-isocyanatopropyl, H 2 N-CH 2 CH 2 NH- CH 2 CH 2 NH-CH 2 CH 2 CH 2 -, (CH 3 O)3Si-CH 2 CH 2 CH 2 NH-CH 2 CH 2 CH 2 - or a group of formula
  • silanes of formula I wherein R is methyl, vinyl, 3-mercaptopropyl or
  • Y ⁇ , Y 2 and Y 3 in formula I are preferably methyl, ethyl, acetyl or 2-methoxyethyl.
  • silanes of formula I are octyltriethoxysilane, methyltriethoxy- silane, methyltrimethoxysilane, tris[3-(trimethoxysilyl)propyl]isocyanurate, vinyltriethoxy- silane, vinyltrimethoxysilane, vinyl-tris(2-methoxyethoxy)silane, ⁇ -methacryloxypropyltri-meth- oxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidyloxypropyttrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimeth- oxysilane, N-( ⁇ -aminoethyl)- ⁇ -aminopropyltrimeth- oxysilane
  • the filler (b) and the silane (c) can either be added as separate components to the resin (a) or, preferably, a silane-treated filler, i.e. a filler which has previously been coated with the silane, can be applied.
  • Silanes containing no reactive groups are generally quite volatile and filler coating is usually carried out in the gas phase by exposing the filler to their vapours. This ensures maximum reaction with the surface and minimum self-condensation.
  • silanes having reactive groups like vinyl or amino groups are less volatile and are usually coated from solution of some sort.
  • the amount of the silane may depend on the type of filler to be used and is generally in the range of 0.1 % by weight to 10.0 % by weight, preferably from 0.5 % by weight to 5.0 % by weight, and more preferably from 1.0 % by weight to 3.0 % by weight, based on the weight of the filler.
  • compositions according to the invention are particularly useful as adhesives having wide temperature operational performance as well as long term usage.
  • the invention therefore further relates to a process for bonding metallic or polymeric substrates which comprises applying a composition containing components (a), (b) and (c) as described above to the surface of at least one of the substrates, bringing both substrates together and curing the adhesive composition by heating the array to 80-220 °C. Best results are obtained when components (a), (b) and (c) are mixed at slightly elevated temperatures ( ⁇ 50°C, preferably 40-45°C). The thus obtained mixtures can be stored at room temperature for a longer period.
  • the mixture Prior to application, it is recommended to heat the mixture to 50-80°C, preferably 55-65°C.
  • the curing catalyst is then added at room temperature or at elevated temperatures up to 80°C. Subsequently, the adhesive mixture is applied to the substrate and finally cured by heating to 80-220°C.
  • a two-component adhesive composition consisting of a resin component (Mix A) and a hardener component (Mix B) is prepared from the following ingredients; the amounts are listed in Table 1 :
  • Blendur I 4516 low-viscosity EPIC resin based on bisphenol A diglycidylether and diisocyanatodiphenylmethane
  • Blendur I 4520 low-viscosity EPIC resin based on bisphenol A diglycidylether and diisocyanatodiphenylmethane
  • Sylosiv A3 molecular sieve
  • Ketjblack EC3005 carbon black DB 03: defoaming agent
  • Mix A is prepared using a Dispermat high speed disperser which can be operated under full vacuum (-0.1 bar) at 1500 rpm.
  • Resins Blendur I 4516 and Blendur I 4520 are mixed with Sylosiv A3 molecular sieves and HXA 5 microglass beads for 15 minutes (-0.1 bar and 1500 rpm). The temperature during this period is allowed to rise and is then maintained at 45°C.
  • Carbon black Ketjblack EC300 J and defoaming agent DB 03 are then added to the vessel, full vacuum applied (-0.1 bar) and the materials dispersed at 2000rpm. The process temperature is allowed to rise and then maintained at 40 °C (Example 1.1 ) or 0°C (Example 1.2) for 15 minutes.
  • Mix B is also prepared using Dispermat high speed disperser operating at 1500 rpm.
  • VPKU3-4523 is blended with BDMA (N,N-dimethylbenzylamine) at room temperature for 5 minutes.
  • Preparation/testing of lap shear specimens for the evaluation of Mix A / Mix B begins with mixing 100g of Mix A with 1g of Mix B; this is one by hand at room temperature. After approximately two minutes vigorous mixing, the material is placed in a vacuum chamber and fully degassed for a further two minutes at -0.1 bar. Aluminium test strips 1 12.5 x 25 x 1.6 mm, previously treated with the laser surface treatment described in WO 96/23037, are placed in a lap shear assembly jig which utilises TFE shims to give a consistent bond line thickness of 0.2mm and overlap of 12.5mm. Adhesive is deposited with a slight excess between the two PTFE shims.
  • test specimens are cured in a fan assisted oven for 1 hour at 200°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition comprenant (a) une résine à base de polyépoxide et de polyisocyanate, (b) une charge, et (c) un silane. Cette composition convient comme forte utilisable dans des conditions extrêmes de températures.
PCT/EP2000/011576 1999-11-22 2000-11-21 Composition pour adhesif WO2001038414A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU21612/01A AU2161201A (en) 1999-11-22 2000-11-21 Adhesive composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9927429.2A GB9927429D0 (en) 1999-11-22 1999-11-22 Adhesive composition
GB9927429.2 1999-11-22

Publications (1)

Publication Number Publication Date
WO2001038414A1 true WO2001038414A1 (fr) 2001-05-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/011576 WO2001038414A1 (fr) 1999-11-22 2000-11-21 Composition pour adhesif

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AU (1) AU2161201A (fr)
GB (1) GB9927429D0 (fr)
WO (1) WO2001038414A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634787A (zh) * 2021-04-25 2022-06-17 上海蒂姆新材料科技有限公司 一种pu胶粘剂及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4070416A (en) * 1972-11-29 1978-01-24 Hitachi, Ltd. Novel thermosetting resin and a process for producing same
US4087414A (en) * 1975-09-16 1978-05-02 Mitsubishi Gas Chemical Company, Inc. Process for producing a flame retardant isocyanurate resin
US4130546A (en) * 1976-10-19 1978-12-19 Hitachi Chemical Company, Ltd. Thermosetting resin composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4070416A (en) * 1972-11-29 1978-01-24 Hitachi, Ltd. Novel thermosetting resin and a process for producing same
US4087414A (en) * 1975-09-16 1978-05-02 Mitsubishi Gas Chemical Company, Inc. Process for producing a flame retardant isocyanurate resin
US4130546A (en) * 1976-10-19 1978-12-19 Hitachi Chemical Company, Ltd. Thermosetting resin composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634787A (zh) * 2021-04-25 2022-06-17 上海蒂姆新材料科技有限公司 一种pu胶粘剂及其制备方法

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Publication number Publication date
AU2161201A (en) 2001-06-04
GB9927429D0 (en) 2000-01-19

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